(2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

Base Information

Chemical Name:(2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate
CAS No.:128360-00-9
Molecular Formula:C₁₂H₂₃NO₅Si
Molecular Weight:289.404
Hs Code.:

Synonyms:(2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

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Chemical Property of (2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

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Technology Process of (2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

There total 2 articles about (2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 2-(Trimethylsilyl)ethyl azidoformate

: 128360-00-9
(2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

Guidance literature:: With triethylamine; In acetonitrile; for 16h; Ambient temperature;
DOI:10.1021/jo00304a035

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 78269-85-9
carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-(trimethylsilanyl)-ethyl ester

: 128360-00-9
(2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

Guidance literature:: With triethylamine; In acetonitrile; at 20 ℃;
DOI:10.1016/j.bmcl.2017.11.005

Reference yield:

: 128360-00-9
(2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

: (2S,4S,5R)-4-Acetoxy-5-benzyloxymethyl-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 65 percent / PPh₃, EtO₂CN=NCO₂Et / tetrahydrofuran

2: 1) Et₄NOTs, 2) Ac₂O, Et₃N / 1) graphite electrodes, 5.5 F mol^-1, 2) CH₂Cl₂

3: 77 percent / AcOH, H₂SO₄

4: 86 percent / TsOH

5: 67 percent / (Bu₃Sn)2 / benzene / Irradiation

6: 82 percent / TFA, aq. NaHCO₃ / CH₂Cl₂

7: 1) O₃, 2) NaBH₄ / 1) MeOH, CH₂Cl₂

8: 91 percent / Ag₂O / CH₂Cl₂ / Heating

9: 72 percent / Ti(O-i-Pr)4 / 110 °C

With sodium tetrahydroborate; sulfuric acid; bis(tri-n-butyltin); acetic anhydride; sodium hydrogencarbonate; tetraethylammonium tosylate; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; silver(l) oxide; diethylazodicarboxylate; titanium(IV) isopropylate; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/jo00305a007